- contact@waywardkeytours.com
CLEARWATER & ST. PETERSBURG FLORIDA
- 727-355-3717
Clearwater & St. Petersburg, Florida
Straight answers about getting out on the water here — what a private charter actually costs, what happens on one, where the good spots are, and whether any of it is worth it for your group.
Most of this is stuff people ask us on the phone. Rather than answer it one call at a time, we wrote it down — including the parts that don't necessarily point toward booking with us.
If renting a boat makes more sense for your group than chartering one, we'd rather you know that before you spend the money.
The questions worth answering before you spend anything.
Real numbers, what's included, and how private charter pricing compares to the per-person tours you'll see advertised on the beach.
See charter pricing →An honest look at what you're paying for and who it genuinely suits — plus who'd be better off on a public tour.
Read the answer →Renting is cheaper on paper. Here's what that number leaves out, and when renting really is the better call.
Compare them →What actually changes when the boat is yours — pace, route, stops, and whether you can stay longer somewhere you like.
Compare them →Practical things worth knowing before you're standing on the dock.
How the day actually runs — meeting up, getting underway, how stops get chosen, and what happens if plans change mid-trip.
Read what to expect →What's worth packing, what's already on board, and the things people consistently forget.
Read the packing guide →Season by season — water temperature, crowds, weather patterns, and when the Gulf is calmest.
See the seasonal guide →What happens if the weather turns, how rescheduling works, and how far ahead you should book.
Read the policy →Birthdays, anniversaries, proposals, bachelorette parties, corporate days — what works on a boat and what to plan for.
See occasion charters →The full list — group size, age minimums, restrooms, alcohol, departure locations, and everything else people ask.
Read the FAQ →What's actually out there, and what nobody can honestly promise.
The honest answer, how often it happens, and why any operator guaranteeing wildlife is telling you something they can't know.
Read the guide →Season by season, plus the time of day that consistently produces the most activity.
See the timing guide →Where they congregate, how they behave, and what the Marine Mammal Protection Act requires of any legal operator.
Read more →The straight answer about what's in these waters, and why it isn't the thing worth worrying about on a swim stop.
Read the answer →Two different coastlines, two genuinely different days.
North toward Caladesi, Honeymoon Island, Three Rooker, and Anclote Key. Sandbars, shelling beaches, and the new island that formed after the 2024 hurricane season.
Things to do on the water in Clearwater →Shell Key, Fort De Soto, Egmont Key's submerged Civil War batteries, and the Sunshine Skyway seen from underneath. More manatees on this side.
Things to do on the water near St. Pete Beach →One page each, for the places worth knowing about before you pick a day.
Regularly ranked among the best beaches in the country, and quieter midweek than anyone expects.
Read the guide →Four miles of beach, a virgin slash pine trail, and the new island off its northern tip.
Read the guide →No ferry, no road. A notable bird rookery and some of the least-walked sand on this coast.
Read the guide →A protected barrier island with some of the best shelling anywhere near St. Petersburg.
Read the guide →A Civil War fort at the mouth of Tampa Bay, with batteries you can snorkel over.
Read the guide →Arriving by water gets you the sandbars and the back side — a different place than the one you drive to.
Read the guide →Where they are, when they're exposed, and why tide timing matters more than the forecast.
Read the guide →You're closer to the good islands than people on Clearwater Beach are. Here's what that changes.
Read the guide →From Captain Keith, on reading the water.
Decoding depth through water color, mud flats, and shallow sandbars — how a captain reads what's under the boat before the depth finder catches up.
Read Captain Keith's notes →A honeymoon charter in Grand Cayman started it. A submarine career, a nursing career, and a stubborn love of warm water did the rest.
Read our story →Every Wayward Key charter is private — your group only, up to 6 guests, no fixed route. Captain Keith is at the helm on every trip.
Gulf Escape
$395
2.5 hours · up to 6
Half-Day Island Escape
$575
4 hours · up to 6
Sunset Escape
$425
2.5 hours · champagne included
